I live in a country that's basically Fashion Nowhere, in a tiny almost-rural suburb, and don't have the money to spend on expensive clothes either, so I've always felt like a "fashion outsider", in every possible way- an outsider both to the regular fashions around me, and an outsider to the fashion world at large.
Basically, what girls wear around here is mainly long flowy tunics over pants, or t-shirts with jeans, and lots of sandals/flip-flops (and maybe Converse low-tops, if they have 'alt' pretensions). When I began college, I was one of the very few girls who wore skirts, but now everyone wears those too- though still with those horrid little fitted t-shirts. It's an eyesore, I tell you. I also wore my dad's old plaid shirt for many years (from 2001 onwards), back when wearing plaid shirts wasn't trendy.
My style's been a cross between ladylike and grungy/super-casual for many years now. I wear the following:
1. t-shirts layered under dresses that would be too revealing without them
2. Men's shirts with pencil skirts/pleated skirts (either short-sleeved, or I roll up the sleeves)
3. Laceup shoes/canvas sneakers for which I change the laces to something more colourful. Sometimes I even wear desert boots/hiking boots
4. Oversized jackets (one of mine is almost like a parka)
5. Blazers/cropped jackets
6. Tights/over-the-knee socks (when the weather is cool enough)
7. Very worn-out loose t-shirts, which I also wear with skirts
8. (recent addition) a pair of olive green 3/4 length cargo pants I've had from the age of 17, which I recently rediscovered- super-grungy, and super-comfortable.
There are other details that I like to dabble in, like ties, hair decorations, braces etc, that most girls around here don't even consider a possibility, too.
I honestly think I'd rather go naked than wear what most girls around me like to wear. All those years when I felt like an outsider because my body began going through puberty when all the other girls around me weren't, have left their mark- I couldn't dress like them when I was younger because it was physically impossible (one could say), and now I can't do it because I'm just so used to not being dressed like people around me. If anyone attempts to give me a long tunic or a pair of flip-flops, chances are I'll burn them
. I'm ok with my outsider-ness now, and frankly, it's a slight source of pride to me knowing that I'm not one of the fashion sheep.
Also, I think I'm perceived as generally 'weird'/intimidating, and I must admit I probably do a lot to encourage it
. Girls walking around in stompy hiking boots and men's shirts with messy hair isn't really considered very 'feminine', haha!